Rob Riggle talks Step Brothers, The Office, 21 Jump Street, The Daily Show, Modern Family, and much more

Welcome to Random Roles, wherein we talk to actors about the characters who defined their careers. The catch: They don’t know beforehand what roles we’ll ask them to talk about.

Rob Riggle has given too many hilarious performances in almost too many projects for people to remember where they saw him first. But comedy has been better off since at least the mid 2000s, when Riggle appeared in Talladega Nights, The Office, Step Brothers, and The Daily Show within a two-year period. Then he proceeded to steal scenes in 21 Jump Street and its sequel, as well as Dumb And Dumber To, Modern Family, New Girl, and more. Riggle also delivered credible dramatic performances in Midnight Sun and 12 Strong, just to prove he’s more than a one-man laugh factory.

Cursed Friends is Riggle’s latest project, a Halloween-themed film for Comedy Central about four friends who discover that a predict-your-future game they played during childhood is wreaking havoc on their lives as adults. In addition to talking about Mr. Knight, the high school teacher who menaces Andy (Harvey Guillén) with his unrelenting niceness, Riggle spoke to The A.V. Club about his considerable history as a joke bomb on TV and film, even among some of the most distinguished comedians working in entertainment.

Rob Riggle: Thank you for mentioning that. The backstory of that was, when I was on The Daily Show, I shared an office with John Oliver, and John was a big standup, very talented. I was not a standup, I was an improv sketch comedian. So I used to drag him down to the UCB because I was a geographical bachelor at the time. My wife and kids were living back in Kansas and I was living in New York. Comedy Central didn’t pay that much, so I was in this little studio apartment and in the evenings I didn’t have anything to do other than to have a burrito bowl at Chipotle and go back to my apartment, play PlayStation and stay out of trouble. So I would go out to the UCB most of the time and do sketch shows or whatever. But I said to John, come with me and just do monologues for ASSSSCAT [one of the longest-running improv shows in the country,] and it’ll be fun. And he’d come down and he could tell stories and he killed it. So then he said, “Well, now you’ve got to come with me to stand up.” I said, “I hate standup. I tried it when I first got here. It stinks.” He said, “Just come with me.” And I wanted someone to hang with back in New York, and you could jump in a cab after work and hit like five open mikes in a night. We were both single or geographical bachelors who had time to kill in the evening, so we would go out and do it. And I remember I was like, “I don’t have any material.” He was like, “Just tell me a story. Has anything happened that’s funny recently?” I said, “Well, I almost killed myself this morning getting out of the shower. I got out and my foot hit the ground and I wiped out. Literally my head almost hit the toilet. It was disgusting!” And he said, “Tell that story.” And that’s the story that you’re mentioning. I ended up telling that story and for a week I just kept telling that story and adding to it and coming up with different things and different details and embellishing and heightening it. And so it turned into about a two-minute bit, and that’s the one you’re describing. And it all started there.

AVC: The A.V. Club was invited to speak to you because of Cursed Friends, so I feel like it’s appropriate to start there. You sort of exist to menace these four characters in a very friendly way. What did you look at with the role and what your thoughts were in terms of playing this character?

RR: I mean, the character’s pretty self-explanatory, but we definitely wanted to make him interesting in the fact that, like you just said, he’s menacing yet approachable, which is a push and pull. So I just tried to do what I always do, which is try to take people from my past that I have had experiences with or that I could draw from and try to find ways to channel that and then heighten it a little bit for comedic purposes. And I was really lucky that we had such a great script, great director, great producers and a great cast. So it just made the whole thing a lot of fun, really. It was easy to do.

AVC: Was it a teacher or somebody in the military that you had been where there was a parallel or personality element that you drew from for this character?

RR: I wasn’t mirroring anybody specifically. It was more of a hybrid of people that I interacted with. I used to have a really super-positive woodshop teacher, who listened to cool music and was always upbeat. You walk into his room, and he was like, “Hey, Rob, what’s going on, man? Get your safety glasses. We got work to do today. I feel great. Let’s do it!” And he was always so super positive. That kind of stuff. And then being menacing, I unfortunately had some menacing people in my life, so I know what that’s like, too. So you just try to find ways to do it comedically. And then, of course, when you’re working with guys like Harvey Guillén, Harvey cracks me up. So I was so fortunate to do most of my scenes with Harvey. So that was just pure joy.

AVC: Working a little bit backwards, I watched you a year or two ago in The War With Grandpa. Unexpectedly, you were just a straightforward, good dad in the context of this heightened scenario. Are you making a shift from being this sort of joke bomb coming into to blow up scenes?

RR: Well, you have to have straight people in your scenes in order for the comedy to pop. If everybody’s crazy in the scene, it goes off the rails, it goes in weird directions. No one’s listening. So there has to be at least one person in a scene that is saying, “Hold on a minute, hey, wait a second. Don’t you think this is a bad idea?” One advocate for the audience. Blue doesn’t stand out against blue. Red stands out against blue. So you have to have a nice base of reality so that the unreal can pop, so to speak. So I love playing the dialed-down straight guy. Because that’s serving the comedy. And I also love playing the the wild one, the crazy one, because that’s going to be a ton of fun as well. But Jason Bateman to me is the greatest straight man of all time. He serves comedy so well, and he’s not out there running around jumping. Because he’s always just being very, very honest, very direct. And he’s always been an advocate for the audience.

Anyway, not to deconstruct and dig down on that too much, but I just want to do comedies. And so if that means I’m the straight guy, I’m the straight guy, because I see I see the value in everybody in the comedy and every role is needed in a comedy, or you can’t have it. So I appreciate just being involved in comedies, whether I’m the straight guy or the crazy one. As far as other work, of course I want to expand as an actor and as a comedian and all those things. So I love doing drama, I love doing comedy, I love doing just straight work, and playing it as real as I can.

AVC: Playing the straight guy versus playing the crazy character, is one of those either more natural to you or more challenging than the other?

RR: Playing big and wild or crazy is always fun, because you get to just shoot the lights out. And that’s usually a part of your personality that you’re never allowed to take out for a walk, so whenever you get to do it, it’s so fun. But the straight man to me, I think there’s a lot of artistry in the straight man, especially a good one, especially if you’re subtle. But at the same time, you have these really honest and genuine reactions and you’re playing at the top of your intelligence. And a good straight man probably doesn’t get the recognition that they deserve. But to me, without him or her, the scenes just don’t work. They won’t ever work in harmony. And that’s why I think a good straight person is worth their weight in gold, to be honest with you.

AVC: Working with somebody like Robert De Niro on The War With Grandpa, who seems like he’s built to be the straight man, what sort of experience is that like to be in the in a room where he is sort of stretching outside of maybe what we would expect for him to do?

RR: I can’t speak for him obviously in any way, shape or form, but I think when you when you live a life in the arts, you want to expand and grow. You want to figure out what your palette has, all the different colors. And obviously, Robert De Niro is one of America’s finest actors. He’s an icon around the world, and it’s because his range is so fantastic. I’ve done sketches with him on Saturday Night Live. I’ve had the pleasure of working with him on The War With Grandpa. And he understands what’s funny about a scene. He understands when he plays a straight guy or when he has to play the wild one or there’s a big, funny set piece that he needs to do. He’s wildly calculating, and understands why something works.

AVC: Going back a ways, your brief role on The Office happened very early in your career. How ready were you for that situation, where there was some structure for the plot but there also seemed to be opportunities for you to sort of play around, particularly with people like Steve Carell, who have such an aptitude for that?

RR: Well, especially in comedy, you have to have a really good script to start with. And then there’s always going to be some improv. Because you just find things in the moment that you didn’t know when you were sitting at a computer or typing it up. You can’t foresee what the set’s going to look like or what somebody is going to say or how someone’s going to react, so improv opportunities are everywhere. And I was blessed. I came up through the Upright Citizens Brigade Theater, so improv was my language, and I always felt very comfortable in that. Now, when I did The Office, I was still very green. Show business, I didn’t have much experience. But with regard to improv, I felt very comfortable. So if I threw out a suggestion or tried a different word or a different look or had a different attitude or did something that might have been a little different from what was on the page, it was usually received pretty well and I was given the green light to keep doing it. So I always felt very good about that.

AVC: What sort of confidence boost was it to land a role on that show opposite all these folks who are so terrific as comedians and actors?

RR: Oh, it’s the gift that keeps on giving. I consider that a highlight in my acting career—to be on that particular episode, too. It was such a fun episode to shoot because we were we were out on filming overnight. Normally when you film on a set, they get ready to move on to another scene or reset the cameras or whatever, and everybody takes a break or goes to craft services or goes back to their trailers. And we were on a boat floating in the harbor, so there was nowhere to go. So when they had to reset cameras, we all just sat together in these booths and told stories and hung out. The whole cast, plus Amy Adams was on that episode, Steve was there, and so it was really a cool opportunity to just sit around and talk and get to know each other and have fun. And I just remember laughing for many, many nights in a row while we were filming that.

AVC: With the pedigree of Upright Citizens Brigade, when you came on to something like Talladega Nights, with an extremely well lubricated group of improvisational comedians and practiced performers, how does that up your game?

RR: Adam McKay is a genius when it comes to comedy and he’s a comedic mastermind. I always enjoyed listening to him and talking with him. And I remember we had met at the Upright Citizens Brigade. He had seen me do improv there, and I think he might have done the monologue when I was performing. So we had known each other for a while. And I was so happy that I got asked to play that sportscaster. That scene was actually bigger—it got cut down for the movie—but I think I did well enough. So I was lucky enough that he asked me to to come in and do Step Brothers. The way Adam works, you can make a whole other movie with the stuff that’s on the cutting room floor. It’s wonderful because it allows you to improvise a tremendous amount. And when you’re working with other actors that love to improvise as well, the scenes go anywhere. You can look at the deleted scenes on the DVD and just see how off-the-rails we went and how much fun we had. We couldn’t even get through some of the stuff because we were just dying laughing—making each other laugh, not on purpose because the other person didn’t necessarily know what was coming, and it would just level everybody. And Adam yells out stuff from video village that you have to sit and process before you can even try to say it. So I always felt very blessed that anytime I get to work with Adam. We did some Funny Or Die stuff for HBO. We did The Goods: Live Hard, Sell Hard. We did The Other Guys. So I always enjoy the opportunity to work with someone who is that talented.

AVC: Step Brothers in particular is such an anarchic masterpiece. Watching you basically want to smash Will Ferrell in the face half the time, can you talk about what, if any, throughline you had?

RR: Well, my role, Randy, there wasn’t a whole lot on the page. But Adam trusted me and was like, “Go for it.” So I would look at the situation, go, what am I? Who am I here? This is all the actor stuff you learn when you go to acting school and you learn how you’re supposed to look at things. And I thought, well, I’m here for Adam Scott. I am his henchman. I am his muscle. I am his sycophant. Whatever he needs, whatever he wants, everything he says is the best thing I ever heard. So if he doesn’t like Will, I don’t like Will. I hate Will. So that was it. I think a dinner scene was the first scene we shot, and Adam got a golf a driver as a birthday gift, holding it and doing Tony Montana, “Say hello to my little friend,” and all of that. And I remember Will did something and I yelled at him to shut up, but it was really inappropriate the way I did it. But I barked it at him and it got a reaction. And Adam Scott loved it. So then I became like a Doberman—I was just always in attack mode and always against Will. And it was totally disproportionate. But that was the game that we created in that moment. And then it just kept working and it made Will laugh. And so you just have to find what the game is, and how you can best serve what’s going on. I didn’t try to be something I wasn’t. I didn’t try to be the intellectual friend who was reasoning with Adam Scott. I’m his henchman. I’m his attack dog. And so I then play the game however I can find ways to do that.

AVC: It was around that time that you also started as a Daily Show correspondent. Each correspondent has a different metric for the balance between exploring political news and just straight comedy. Was that purely a comedic opportunity for you, or was it an opportunity to filter in political commentary?

RR: I don’t like to go down those paths of overthinking this stuff. If you start deconstructing comedy, if you start plugging in politics, if you start propagandizing or putting in messaging, you know, I think there’s always a place for that. Look, I love George Carlin. My first album was A Place For My Stuff. But I like to be more in the moment more, react more. What would this character do? “What’s the best thing this character could do at this moment” is usually what I’m thinking, or, “What’s the most obnoxious thing this character could do at this moment,” and then execute from there. But I don’t try to read or preplan too much because deconstructing comedy or intellectualizing comedy sucks the comedy out of it.

AVC: How important was the actual news reporting part of your job in that role as opposed to just being a “character” who could do funny shit?

RR: Jon Stewart was the first one to say and he would say it often and he would say it loud and said it everywhere he went, we are not the news. Do not come to us for the news. Go to the news for the news. We are a comedic show. We follow puppets that make prank phone calls. And a lot of people did tune in to Jon for the news and for their truth, but Jon would be the first one to tell you, don’t do that. Now, Jon is a genius and he’s got strong political views. And so he takes his unbelievable comedic genius, and he puts it together with his passion, and he makes magic. And a lot of people can do that, in a lot of different ways. Colbert did it in a really fun way. And some people do want a break from it, and just be tickled by noticing the absurdities of reality. I tried not to wield too much politics in the comedy that I do. Sometimes it’s unavoidable, something needs to be commented on. If there’s an elephant in the room, you’ve got to comment on it. But otherwise I just try to have fun, that is hopefully the kind of fun that everybody can enjoy.

AVC: The original Hangover is a classic, and the scene with you and Zach Galifianakis is pretty unforgettable. Todd Phillips has this uniquely misanthropic sense of humor that is really different from, say, Adam McKay’s humor. Do people have different comedy styles that work better or differently for you in your performance?

RR: I’m really blessed because Adam McKay always gives you the freedom to improvise, so you never have to worry, should I try this or should I not try this? Because when you’re on set, time is money. You don’t have time to sit there and experiment. And you might not be very high on the call sheet, so who are you to come in there and say, “I’m going to rewrite this because it’ll make me sound funny?” You’re part of a team, you’re part of an ensemble, and if you do have something that you think you contribute, okay, give it a shot. But you don’t always get that opportunity. But Will and Adam were both very gracious writers, directors, and actors, and they were always willing to hear what you had to say. And if they thought it would fly, they’d say, “Give it a shot.” And more times than not, it would fly.

It was the same with Todd. I knew Todd from back at the UCB. So he had a great appreciation for improv and he was willing to let you throw out a couple of things. And so I found myself in The Hangover adding things, because to me there was this dead space, so I thought I would have some fun and fill it in with a couple of thoughts. And it worked. And he was like, “That was great, do it again.” And it fills you with confidence and it makes you feel like you’re on the same page. And so it’s a real blessing to work with actors and directors that that are not averse to improv, because I think you could find a lot of good stuff that way. Jonah Hill was the same way when we did 21 Jump Street. He was all about, hit me with something that I don’t see coming. And we would do goofy things in the moment and find really fun things that were not on the page, but made the film.

AVC: You mentioned 21 Jump Street, where you had the infamous opportunity there to get your dick shot off. Not everybody has that chance in their career. Phil Lord and Chris Miller seem so astute in giving people a lot of freedom and also to operate within these very self-aware boundaries of the genre. Was there any guidance they gave you for playing a teacher who ends up being a criminal mastermind?

RR: Not really. I mean, it was never heavily discussed like this. I had the script. I knew what the scenes were. I knew who the characters were. So then we just get in there and start playing within that structure of the script. And we would find things. So there was no sit down and analyze it the night before. Everybody showed up ready to go and in good spirits. And generally speaking, the joy came through.

AVC: When you read a script that says at the end, “my dick gets shot off,” what is your immediate reaction to that?

RR: Well, all it said was I got shot in the dick. Now, while we were filming, I screamed, “Oh my God, that’s my dick,” and it made the crew laugh. It was late night shooting. We were racing against the sun because that was the end of our week and we had to get the shot and everybody was exhausted. And I screamed and made everyone laugh, and we got some energy going again. Then it turned into, okay, now what? Now I’m handcuffed, I can’t grab it. So I asked them to grab it for me. They say no. And again, this is all improvised. And when I went down to grab it with my mouth, that was a suggestion from Jonah. But there was nothing to grab, so they went to crafty and got a banana and they covered it in blood, and then I grabbed that. But when I came back up, I actually bit through the banana. So it popped back out of my mouth and we’re all laughing and improvising. None of it’s on the page and we’re having a blast. And I’m thinking to myself, this is good because it’s good energy where everybody’s kind of waking up. We’re getting our second wind. But surely the good people at Sony aren’t going to put this in the movie. It’s too dirty. Well, that’s the thing—you improvise it, they get it on film, it gets a big laugh, it makes the movie.

AVC: I did want to ask about The Other Guys, where you’re sort of an intermediary between the other guys and the super cops of Dwayne Johnson and Samuel L. Jackson. Was there a movie cop or a real authority figure who you drew upon for this bravado and ambition, however mean spirited as it might be, towards Will and Mark?

RR: Oh, yeah. It’s an amalgamation of every football coach I ever had, every drill instructor I ever met. There’s a lot of hard-core masculinity in some of the worlds that I’ve been in. So you draw from everybody. And then I know what it’s like to be in a locker room, to be a part of a team. I know what it’s like to be these characters. But everybody was the other guys. If you weren’t The Rock and Samuel Jackson, you were the other guys. The whole squad was the other guys. And we were all jockeying to be the next big boy. So what goes along with that? It doesn’t matter if it’s men or women, doesn’t matter if it’s a school, faculty or an NFL team. Everybody’s trying to jockey to be top dog. And in the process, you’re always going to find people who are insecure. And that insecurity always comes out. It comes out in the form of bullying, snide comments. It comes out in the form of posing. It’s the study of you of being human. So, again, you take all those things like any actor does, you look at it, think about it. Try to remember moments in your life and you try to personalize it. Try to find the truth of what your character’s doing. And then then you try to put a comedic stamp on it and send it out there.

AVC: In that case, what personal experience did you draw upon to be in a situation where you say, “I took the belt off my neck and went home, the next morning?”

RR: That actually didn’t happen [laughs]. We were being pulled on a trailer around New York in a car, and Damon and I were just filming. And quite literally, Adam was up in the truck and he had a walkie talkie and he was like, “Just talk about anything you want to talk about.” And, again, you can make another movie off of the stuff that was cut out of there. But we were just saying anything that we could to be obnoxious, be ridiculous, say crazy things. Things that don’t make sense, but say it sincerely. And so that’s what we did. We were just saying things to try to make each other laugh.

AVC: You landed a long-term role on Modern Family. Can you talk about playing a role for a long time?

RR: It was very simple for me. I was Phil Dunphy’s nemesis, period. So what does that mean? That means everything that goes along with being someone’s nemesis. I show up at his door at his lowest moment. That’s when I pop in. It’s the moment when you’re standing in a rainstorm and a car drives by and splashes you with a wave of water, and now you’re completely soaked and the flowers you’re holding are wilted. And you look down and the dog’s peeing on your leg. And it can’t get any worse, and then all of a sudden I show up. That’s how it could get worse. So what I envisioned was, whenever Phil’s up against it, that’s when I pop in. Because what could be worse than to have Gil Thorpe show up at your worst moment, especially if you’re Phil Dunphy. And that just meant any form of agitation, any form of difficulty that I could put on Phil Dunphy’s shoulders. It was my responsibility to do that. And of course, I didn’t have to do much. The writing was as good as it gets.

AVC: How much do you rely on the script or the director to know how far to push something?

RR: It’s all situationally driven. You have to know the show, know the people, know the characters. What seems reasonable? What doesn’t seem real? What are they going for? Sometimes they have you saying something in the scene and you’re like, do I really have to do this or say this? And in the big picture, we need to be this harsh or you need to be this way because it makes the payoff at the end bigger when he pushes back against you or whatever. And you’re like, okay! So it’s all of that stuff that you just mentioned is case by case and day by day.

AVC: 12 Strong was obviously a straightforward dramatic role, and also one that to some extent leveraged your experience in the military. Has your military experience materially helped you throughout your career? Or was that a fairly isolated opportunity?

RR: No, I had done what I would consider a very dramatic role in a movie called Midnight Sun with Bella Thorne. That was a role I would classify as dramatic. What I did in 12 Strong was what I would consider a straight role where it’s not heavily dramatic, but it’s very straightforward, very real. So I kind of put them in different categories in my own mind. But 12 Strong was very personal for me because I was playing Lieutenant Colonel Max Powers, who was the commanding officer of Third Battalion Special Forces Group. Now, when I personally went to Afghanistan as a young captain of the Marine Corps, I reported to Colonel Max Bowers, and I was on his staff. I used to brief him every morning and every evening. So I knew the man personally. I served with him. And then to play him in the movie was, to me, quite an honor. The movie ends with them taking a city called Mazār-i-Sharīf up in the north of Afghanistan. Where the movie ends, about a week later is when I ended up joining a unit in Mazār-i-Sharīf. So I felt very connected to this particular story. I felt like I knew some of the guys personally. So having the opportunity to be part of that movie was an honor. Now, I’m not a war fighter. They were. I was much more of a staff officer. But still, it was an honor to be part of that particular story, because I knew the story for 15-plus years before it was turned into a movie. And it was classified for a while, a lot of what they did. So I was just happy to see that these particular heroes got to have their story told, because it was a fascinating story.

AVC: You mentioned Midnight Sun, which taught you to differentiate dramatic roles from a straight role. Are there specific opportunities that you’re trying to take advantage of to showcase your versatility, or challenge yourself creatively?

RR: Absolutely. I can’t speak for anybody but myself, but in the conversations that I’ve had with other artists, with other actors, anybody who has a life in the arts, you have certain strengths. But you want to see what else you’re capable of, and you want to expand. You want to grow as an artist. You want to grow as an actor. You want to grow as a comedian. And so you want to take on different roles. It’s a natural instinct. Now, can you do it? Well, that’s what we’ve got to find out. Will the audience accept you? I don’t know. Maybe over time you can do it enough. I remember Bill Murray made a movie in 1981 called Razor’s Edge, playing a World War I veteran who was suffering from PTSD and was drinking a lot. And there was a scene in a pool where he was lamenting about his hardships and his pain, and people were laughing in the audience because it was “Bill Murray.” They thought, “Hey, he’s going to make me laugh.” And when a comedian that you love who has been making you laugh for many, many years steps on the screen and he’s not trying to make you laugh—he’s actually emoting something that’s very painful or talking about some heavy stuff—it’s hard for the audience to recalibrate sometimes.

And so it takes time for the audience to warm to seeing you in a different light. Will they allow you to be seen in a different light? You can’t let that determine whether or not you’re going to do dramas or comedies or whatever. You have to do what speaks to you. But there’s a lot of elements that are involved in how it’s received, and when it’s received, when’s the right time to do things. For me, I want to see what I’m capable of. I want to know what I can do. And also, I read things sometimes that touch me or they make me think, wow, I really empathize with that character. Or I really felt that person’s pain, or some connection you have to the piece, and it makes you say, I really feel like I could bring this character to life in a way that is truthful. And when you do that, I think you’re doing what you’re supposed to be doing. I know a lot of amazing dramatic actors that just want to do comedy, I want to do this, do that. And then some comedians are dying to do dramatic work. So it’s a matter of opportunity too. If I don’t get the opportunities, it’s kind of hard. But I think everybody wants to grow and get better and see what they’re capable of.